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Carbocations

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...

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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.

Carboxylic Acids to Acid Chlorides

Carboxylic Acids to Acid Chlorides

Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.

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Updated: Jun 16, 2025

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

Published on: October 3, 2014

(Phosphino)(stannyl)carbene.

Rui Wei¹, Xin-Feng Wang¹, Chaopeng Hu¹

¹Department of Chemistry and Research Center for Chemical Biology and Omics Analysis, College of Science, Southern University of Science and Technology, Shenzhen, China. liuleoliu@sustech.edu.cn.

Chemical Communications (Cambridge, England)

|August 20, 2024

Summary

This summary is machine-generated.

Researchers synthesized a novel (phosphino)(stannyl)carbene, which exhibits ambiphilic properties. This unique carbene reacts with small molecules to form rare stannylketenimines and stannylketene compounds.

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Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

Area of Science:

Organometallic Chemistry
Carbene Chemistry

Background:

Carbenes are reactive intermediates with diverse applications.
Ambiphilic carbenes, possessing both nucleophilic and electrophilic character, are of significant interest.
The development of novel carbene structures with unique electronic properties is crucial for advancing synthetic chemistry.

Purpose of the Study:

To synthesize and characterize a novel (phosphino)(stannyl)carbene.
To investigate the reactivity of this ambiphilic carbene with various small molecules.
To explore the formation of new organometallic compounds.

Main Methods:

Synthesis of the (phosphino)(stannyl)carbene precursor.
Reactions of the carbene with cyanide, isocyanide, and carbon monoxide.
Characterization of the resulting products using spectroscopic techniques.

Main Results:

Successful synthesis of the (phosphino)(stannyl)carbene.
Demonstration of the carbene's ambiphilic nature through reactions with electrophiles and nucleophiles.
Isolation and characterization of rare stannylketenimines and a stannylketene.

Conclusions:

The (phosphino)(stannyl)carbene is a versatile building block in organometallic synthesis.
The ambiphilic nature of the carbene facilitates unique reaction pathways.
This study expands the scope of carbene chemistry and provides access to novel organotin compounds.